


Act of the Demon

by WaywardWinsister



Category: Supernatural
Genre: Anal Sex, Blackmail, Blood and Violence, Brother/Sister Incest, Bruises, Chains, Creampie, Dark Dean Winchester, Dead Dove: Do Not Eat, Demon Blood, Demon Dean Winchester, Evil Dean Winchester, Explicit Language, F/M, Forced Orgasm, Heavy Angst, Hurt Sam Winchester, Kidnapping, Knifeplay, Knight of Hell Dean Winchester, Manipulation, Non-Consensual Blow Jobs, Non-Consensual Bondage, Penis In Vagina Sex, Punishment, Rape, Reader is a Winchester (Supernatural), Reader-Insert, Rough Sex, Sadism, Sexual Assault, Sibling Incest, Smut, Threats of Violence, Torture, Twins, Vaginal Sex, Winchester Sister
Language: English
Status: Completed
Published: 2020-10-31
Updated: 2020-10-31
Packaged: 2021-03-09 02:36:11
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 1
Words: 9,349
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27317119
Author URL: https://archiveofourown.org/users/WaywardWinsister/pseuds/WaywardWinsister
Summary: After being resurrected as a demon, Dean abandons his younger siblings.You and Sam finally track him down to another town and insist on there still being good inside of him.Dean decides to show you both why that just isn't true.
Relationships: Dean Winchester & Sam Winchester, Dean Winchester/Sister!Reader, Sam Winchester & You
Comments: 5
Kudos: 72





	Act of the Demon

**Author's Note:**

> This was inspired by Demon!Dean and spooky season! Halloween special!  
> I know it's messed up, but I'm a sucker for dark fics.
> 
> Follow me on Tumblr @wayward-winsister

“We’re sure that he's here?” You asked, leaning against the side of the rental car that you and your brother were using.

Something didn't feel right to you, but then again, nothing had since Dean had been corrupted.

You surveyed the road and watched different colored vehicles drive both ways for a moment before you turned your head towards the back of the car where your twin was.

“This is where everything is pointing to,” Sam said as he rifled through the trunk before slowing his movements and turning towards you, “It’s our only thing to go off of.”

“I know, and I want him back as much as you do, Sam. I really do, but I also don’t want us to be chasing our asses with this again,” You said.

He let out a sigh as he thought about your words. It wouldn’t be the first time Dean had thrown his younger siblings for a loop, but these situations and places that he led you both to were becoming more dangerous every time.

You knew that demons liked to play games, but this was downright messed up.

“It’ll be okay. We’ll get through it, just like we always do,” Sam said, stopping his gathering to look at you with sincere eyes.

You nodded at him before shifting your sight to the ground in front of you. You had already lost your oldest brother to something evil, so you didn’t think you could handle it if anything happened to your twin, especially if it was something caused by Dean.

You guessed— _hoped_ —that Sam felt the same way about you.

A slam of the car trunk drew your attention back to your brother, who was motioning for you to join him in the motel. You grabbed your bag from his outstretched hand before following him to the ground-floor room.

You stopped shortly and took a slow glance around the parking lot. You didn’t like being here, and every hunter instinct you had was telling you to run, but you wouldn't give up on Dean.

_Not for anything._

You wondered if Sam felt the same about the unnerving energy, or if you were just tense from lack of sleep.

A snap behind you caused you to wheel around, one hand reaching for the knife in your boot, but you hesitated when you saw nothing there but a few empty parking spaces.

You took a step forward with narrowed eyes before the sound of Sam calling your name caused you to set aside your nerves and follow him into the motel room.

* * *

“You hungry?” Sam asked.

A rumble of your stomach answered for you, causing a chuckle between the two of you.

“I think I saw a pizza place on our way into town,” He said as he typed the location into his laptop to find the phone number.

“Oooh,” You hummed. “That sounds good.”

Sam smiled before picking up his cell phone. “You want your usual?”

You nodded before glancing towards the bathroom, “I think I’m gonna go shower and try to clear my head.”

Your twin nodded at you before hearing someone answer his call. He began placing the order as you gathered clothes to take into the bathroom.

Tuning your brother’s voice out, you closed the door and let your head fall back against it with closed eyes. 

_Deep breaths._

You moved in front of the sink to stare into the mirror.

 _Damn._ You looked rough.

Shaking your head, you thought about all the leads and details that had pointed you and brother to this small town. Something definitely wasn’t right, and you were so deep in thought that you almost didn’t notice yourself white-knuckling the edge of the countertop.

Leaning away from the mirror, you walked over to turn on the shower. Setting it to the hottest setting— _which still wasn’t very hot for a motel_ —you began removing your clothes before your brother’s voice caught you off guard.

“Hey, Y/N/N,” Sam said through the door, “The place isn’t delivering, so I’ll go pick it up and be right back.”

You thought for a moment before swallowing, “Be careful.”

“I will. Call me if anything happens.”

“You too,” You said before discarding your clothes in a pile to the side and hopping into the shower.

_Hot motel water and cold nights. The life of a hunter._

* * *

After wiping the steam off of the mirror, you took a step back. You did feel a little better after that shower, but you still couldn’t shake the uneasy nerves that plagued you.

A growl in your stomach reminded you of the pizza that should be back any minute. Taking a deep breath and one last look at yourself in the mirror, you exited the bathroom with your dirty clothes in hand.

Taking a glance around the room, you noticed that Sam still wasn’t back yet. Sighing, you threw your clothes to your bag that was still on the bed that you claimed. You checked your phone for any notifications before setting it on the table between the two beds.

You shoved your bag to the side and laid, stomach down, on the bed. After hours of being a car, it felt so good to stretch out. You let your eyes flutter shut as you zoned out, finally thinking about something other than your brother for once.

The sound of the motel door being opened caused a small smile to grow on your face. You could practically taste the pizza already.

“I was almost starting to get worried,” You said to Sam, eyes still closed.

Just a few more moments of relaxation and then you’d eat.

You didn’t hear your brother respond, so you called his name, “Sammy?”

You were about to turn over and look when a cold chuckle traveled through the air, “Not exactly.”

You immediately tensed. You knew that laugh. You knew that voice. You’d grown up with both of them. You’d been around them all your life, but you had to remember that _this_ was not the same person.

 _That_ person died and _something else_ took over.

Twisting over, you met the origin of the voice with wide eyes.

And there he stood, like a predator eyeing his prey, with cold eyes and a dark aura.

 _Dean Winchester._ The Righteous Man turned demon. Your older brother.

You watched him carefully before quickly glancing at the handgun on the table beside him. A handgun that would do you no good, but you always thought better with a weapon in your hand.

_John had made sure of it._

He followed your line of sight before looking back to you and raising his eyebrow, almost as if daring you to try and make a move. Taking a step closer, his movements caused you to spring to your feet and stand in front of him. Your eyes quickly went to your phone on the bedside table.

You had to call Sam. There’s no way you could take Dean down on your own, but maybe you could buy yourself enough time to escape.

“Oh, come on now, sis,” Dean smirked, an evil glint in his eye, “Where’s the love?”

You shook your head before spitting at him, “Fuck you.”

He chuckled darkly at your words, “Careful what you wish for.”

You swallowed and tried to brush off his threat. He just wants to get under your skin.

_Don’t let him._

You sneakily attempted to locate a weapon while keeping your brother’s attention occupied, “Why are you here?”

You didn’t even mean ‘here’ as in the motel, but more so the town he led you to. You knew that Dean had let you and Sam find him. That was one of the reasons you’d been so tense, and you guessed that Sam knew it too, but no one had brought it up.

Maybe someone should have, because now look where you were.

Face to face with the demon. Your own brother.

Dean decided to humor your question as he slowly stalked towards you, “You and Sammy just can’t stay out of my hair, can you? You both always were in my way, so I guess nothing’s changed. Only that I can actually do something about it now.”

His eyes flashed back, matching the dark undertone of his words. Your heart rate increased at the sight. Every step he took forward, you took backward.

_Deep breaths. Stay focused. Find the right weapon. Panicking will get you killed._

Your father had instilled the words into you ever since you could walk, and always told you to live by them when hunting. You just never thought that your brother would be one of the things that went bump in the night.

But then again, Winchesters had always walked the line between human and monster.

“Where’s Sam?” The words came flying out of your mouth.

Dean stopped and glanced at your frame up and down with a smirk, “Oh, don’t worry about him. You’ll see him again.”

“I’d like him to remain in one piece,” You growled, referring to the last time you’d both gotten close to Dean, only to end up with a knife in your twin’s side.

“Don’t give me ideas, sis. You, on the other hand, could use some adjusting,” Dean chuckled darkly. “Now, we can do this the easy way or the hard way.”

Before you had time to decipher his meaning, he was on you with one hand around your neck. You thrashed and kneed him in the stomach, only for it to have no reaction.

_Damn demons._

You tried to maneuver your body to use your weight to swing him down, but he quickly grabbed your arm and pulled when he saw you begin the movement. You fell to the ground before attempting to crawl forward to reach Sam’s bag that was on the ground.

“Hard way it is? You always did know me so well, sis.”

You felt a bruising grip around your ankle before you felt yourself being pulled backward. You instinctively began to kick and then felt yourself being pulled to your feet. Not being able to see him behind you, adrenaline set in, and you randomly swung, hoping to hit something. You let out a cry of pain as your brother grabbed your arm and twisted before pulling your back flush against his chest.

“Did you forget that I taught you all your tricks, Y/N/N? Don’t make this harder than it needs to be,” He whispered against your ear, holding you tight against him as you thrashed.

“Go to hell,” You growled, hoping that your voice didn’t sound as weak to your brother as it did to you.

He chuckled into your ear, sending shivers down your spine, “Where do you think I came from?”

Your breath hitched and you tried to shake out of his grasp, but felt yourself start to panic when one of his hands came up to grab onto your neck.

You tried to elbow him and do all the moves you’d practiced before, but they were all almost useless on a demon without a weapon.

All those self-defense classes you took. All those sparring sessions. All those instances where you’d been pinned like this.

You would never have considered that your brother would be the one to push you over the edge, but his tightening grip was slowly increasing your worries with every passing second.

“Dean,” You tried, “Stop.”

You only felt a mix of a chuckle and demonic growl against your back, before you tried to claw at him as black spots clouded your vision.

Your struggle was useless as the lack of oxygen caused your limbs to fall limp. Your breaths became short and ragged as he tightened his hold around you.

No. _No._

The last thing you registered before blacking out was the sound of his deep laugh against your ear.

* * *

Sharp pain in your head awoke you from your sleep. You felt it before you opened your eyes, but it wasn’t until you felt something sting your skin that your breath left you in a rush.

Blinking away the blur, you finally noticed that your sight was aimed at your lap.

You were on the floor. _A dirty floor._

You groaned at the pounding in your skull and ache on your body before hearing something move in front of you. The sound of metal on metal immediately drew your attention, as did the muffled words. Looking up, your eyes went wide.

 _There was Sam._ Less than a few feet in front of you. Gagged and tied up in a chair. Staring at you with matching wide eyes.

“Sam!” Your voice came tumbling out of you before you could stop it.

Your words echoed around the empty room, and your twin tried to respond through the fabric around his mouth, but to no avail.

You could see cuts and marks lining his face, and instinctively tried to go towards him, but your movements were cut short by something wrapped around you.

Your back was against a metal pole near the center of the room, and upon closer inspection of your restraints, you noticed that you were bound with chains, rope, and barbed wire.

No wonder you were hurting so much. Someone wanted to make sure that you weren’t going anywhere.

Looking back to your brother, you noticed that his restraints were the same, only they seemed to be much tighter. With sad eyes, you gave him an apologetic look before panic set in.

With adrenaline finally bringing you clarity, you noticed that you both were in a warehouse. An old warehouse too. It looked abandoned and unused. 

Looking around for any other people, you finally began putting the pieces together.

The events of the motel came rushing back to you in flashes.

_Dean. The fight. His laughter._

This was all him. This is why you’d been so paranoid and on edge. This was all a trap.

You and Sam had walked right into the belly of the beast. _Willingly._

“Are you okay?” You asked, turning your attention back to your brother.

He nodded at your words, although his injuries suggested otherwise.

You intended to make the most out of the fact that you weren’t gagged, but you could exactly get detailed responses from Sam, either.

“Where’s Dean? This was him, wasn’t it?”

Your twin moments halted as his eyes shifted to the wall behind you. Your eyes creased before your face fell at the sound of something moving behind you.

Turning your head as far as you could without injuring yourself further, you heard the sound of footsteps along the concrete floor.

You watched as Dean strode past your side to stand in between you and your twin. The bastard was behind you, watching the entire time.

“Finally awake, eh sis?” He turned towards you.

“I would say that I was bored, but Sammy kept me occupied,” Dean said, throwing a wink at his brother.

Sam scowled at the action. You hated thinking of what your twin had to go through, because those marks on his face were more than enough to make you shudder. Especially since you knew that Dean had created them.

“I was beginning to think that you finally bit the dust,” Your older brother said, shifting his attention back towards you.

“You’d probably like that, wouldn’t you?” You growled at him.

You were beyond pissed at this situation, but your anger didn’t do much to calm your fear.

“And have you miss the best part?” Dean smirked. “Someone hasn’t had their adjustment, yet.”

“Was that fight at the hotel not enough for you?” You said, swallowing back the bile that was making its way up to your throat.

“That wasn’t a fight, Y/N/N,” Your older brother’s eyes traveled down to your neck, most likely admiring the bruises he left, “The real fun is about to start.”

“What?” You asked.

He smirked at you as he drew out a knife from behind his back. You watched him carefully as he walked behind you until he was out of eyesight.

Before you had time to question his actions, you felt the cold edge of the blade press against your neck. You heard Sam’s muffled protests as your hair was pulled back against the pole. You felt Dean’s breath against your ear before his eyes shifted from your head to his brother.

“Just wait until you see what I got in store for our sis, Sammy,” He said, a sick smile covering his face.

You heard the scraping of Sam’s chair on the floor in retaliation, and you tried to wiggle away from the demon behind you, but he had a tight enough grip of your hair to keep you in place. You felt the blade run along your cheek back to your ear as Dean leaned in closer to whisper something.

A low enough voice to where Sam couldn't hear but instead see the paling of your face and fear in your eyes. Your twin looked at you with wide eyes as your own tears threatened to spill over.

Your voice came out broken, “No! NO!”

Your only response was a dark chuckle before you felt him move away. As your mind raced around his words, you felt your restraints loosen enough to be freed. Before you could make a move, a groan instantly escaped your mouth as Dean suddenly slammed your head back against the pole before pulling you upwards by your hair. You could hear Sam’s muffled protests and clinking restraints as your older brother tugged up to your feet.

“No! Get the hell away from me!” You screamed.

“You know, Sammy, you and Y/N/N seem so persistent on there still being good in me,” Dean said as he glanced at his younger brother before twisting you to make you look at him. With one hand still in your hair, he tightened the other around your chin to forcefully tilt your head up to look at him, “Now we’re gonna see why that’s just not true.”

“You’re bluffing,” Your voice came stumbling out of you before you could stop it.

_Damn those stubborn Winchester genes._

You felt Dean’s hand move down to your neck and cover old bruises before he gave a tight squeeze and pulled you towards him.

“Let’s find out,” He growled, as his eyes flashed black.

You felt your heart drop at his words before he suddenly gave a kick to your leg and brought you to your knees. A groan escaped your mouth as pain traveled your body.

You heard Sam’s moments nearby. He couldn’t have been more than a few feet, and you hated when he moved because there was no doubt that those restraints weren’t the softest.

You closed your eyes and tried to shake away the panic.

_This couldn’t be happening._

The jingle of a belt buckle made its way to your ears, and you did your best to hope that it was just your imagination playing tricks on you.

You instantly felt a sharp slap to your cheek that swung your head to the side. Trying to shake away the sting that traveled along your skin, you looked back up at your brother, who now had his belt tightly gripped in his hand.

You heard Sam’s muffled cries nearby.

“What was that, Sammy?” Dean asked, a heavy smirk present as he looked over at his younger brother. “Again?”

You heard your twin’s concealed words once more before you heard Dean’s laugh.

“Sorry, sis. Looks like he’s finally turned his back on you.”

Before you could say anything, you felt two hits come to your other cheek. The force was enough to throw you to the side. You felt your stomachs turn before you shook your head and leaned back up.

“Is that all you got?” You growled.

“Just getting started, Y/N/N,” Dean said, before he reached to yank your hair back again, “Don’t forget that I did my time in hell, sweetheart. I know pain.”

You tried shaking your head free, but he held you still. You finally looked at him, and your eyes held a heavy discontent look in them. You hated seeing this thing in front of you.

You had to hope that Dean was still in there somewhere. You had to hope that he wouldn’t go through with what he was hinting at. You had to hope that everything would turn out okay.

You had to hope, because if you didn’t, then you didn’t know if you could survive this.

“How many attacks did I save you from, sis?” Dean said, forcefully tilting your head up once more to look at him.

You held your tongue and only gave him a tear-filled glare before he chuckled.

“Too many. Right,” He said, as he tightened his grip around your jaw, “Maybe it’s time I take one back.”

You removed your eyes from Dean’s and looked over at your twin with an apologetic glance. You could see the confusion in Sam’s eyes at his brother’s words, and it wasn’t until he heard the zipper of Dean’s jeans that he finally understood what he meant.

_Attacks._

You’d once told your brothers that one of your worst fears was getting caught off guard and having someone, especially a monster, defile you in the most disturbing of ways.

They swore that they’d always protect you from that. 

And now, here you all were.

“Dean,” Your voice cracked.

You watched him walk over to the pole where you’d been tied up not minutes ago and grab a heavy chain off the ground. The sound of it being dragged across the floor sent shivers down your spine, and you would have tried to make a run if your twin wasn’t right there.

You wouldn’t leave Sam. You couldn’t, but _damn_. You didn’t know if you could make it through this, either.

You watched him walk behind you before you felt a sharp tug on your hair and your arms uncomfortably pulled backward. You felt the rusty metal being tightly wrapped around your wrists before you heard the click of a lock.

He released the chain, before circling you slowly and smirking at your position. He came to a stop in front of you and started reaching back for his zipper. You immediately twisted your head to the side and refused to face him head-on.

You didn’t face towards your twin, no, because you didn’t want him to see the tears that were threatening to fall.

“Aw, come on, Y/N/N,” Dean said, no doubt enjoying the sight of you in front of him, “What happened to the love you had for me? Remember how you couldn’t ever go anywhere without your big bro?”

You refused to acknowledge his words and instead kept your eyes on the wall. A dark chuckle erupted from Dean before you heard the shuffling of fabric and you squeezed your eyes shut at the sound.

“Maybe Sammy took over for me, huh?” He said, and you tried not to give in to his words.

He was just trying to get a rise out of you. He was playing dirty, like most demons.

_Don’t let him win._

You’d been kidnapped and tortured enough that you were used to comments like that from monsters, but it hit differently coming out of your brother’s own mouth.

“Oh, come on, who knows what kind of things you two get up to alone with each other?”

His words caused you to flinch, and you knew he saw it. You could practically feel him smirking at you.

“Eh, Sammy?” Dean turned toward his brother. “You fuck our sister good?”

You shook your head hard at his question before you could stop yourself.

You hated that he was getting to you like this. All of the brutal interrogations you’d been through. All of the sick monsters that had tortured you. None of them were able to draw such a reaction out of you so quickly. You hated that he was getting exactly what he wanted, and there wasn’t a damn thing you could do about it.

“I bet you enjoy it, too. Huh, sis?” Dean asked.

His voice held a sick and sinister tone, and you couldn't help the ill-feeling that grew in your stomach at the sound of it.

You refused to look at him. You refused to let him see the tears that threatened to fall and the fear in your eyes.

You hoped that his words weren’t affecting Sam as much as they were you. Hell, you _prayed_ that your twin wasn’t feeling as sick as you were, however, his silence caused you to doubt it.

“Why don’t you show me just how much you enjoy it?” Your brother’s voice was twisted.

You squeezed your eyes shut and held your body still.

A growl escaped Dean’s mouth before you felt your head being twisted back to the front. He had a tight grip on your hair and fingers digging into your skin.

You kept your eyes shut as you felt your face being pushed closer to his crotch. You tried pulling away in disgust, but without the use of your arms, your strength was utterly useless compared to your brother’s.

“Come on, now, Y/N/N,” Dean hummed. “Open those pretty little eyes for me, before I do it myself.”

A sharp slap to your cheek after your refusal caused you to finally give in. Your eyes widened at how close he was to your mouth, and at his erection that was growing every second.

“Open,” He commanded.

You didn’t have the strength in your voice to speak, but the panic in your eyes spoke for you. With words getting lost in your throat, you violently shook your head and tried to lean back. The grip in your hair tightened, as your head was shoved back forward.

The head of his cock brushed against your lips, and your tears fell soon after that.

“Really, sis?” Dean mocked. “I was expecting you to last a little longer than that.”

You barely registered his words, before he moved a hand down your face. You felt him trail his fingers through your tears before landing on your jaw. Your breath hitched, as he slowly tightened his grip. Holding your breath, you let another tear fall as your eyes fluttered shut.

You had gone head-to-head with the Devil before, but that was nothing compared to this.

Then, you had hope, because you all were together.

Now, look at you.

A tight grip jerking your head upwards. Your eyes widened at the sudden movement, and your sight came to rest upon your brother’s face. Well, it would’ve been your brother’s face, if it wasn’t for the sadistic grin and obsidian eyes.

“You’re gonna take my dick just how I like it, sweetheart.” He chuckled darkly. “Because if you don’t..”

Thoughts of what he was going to threaten ran through your head.

_Rape. Torture. Murder._

_Whatever._

This wasn’t your first rodeo, and you were beyond pissed with the situation, so let him try whatever he wanted. You didn’t know if you could take it all, but you wouldn’t give him the early win. That wasn’t the Winchester way.

Streaks of tears lined down your face, and you knew that your skin would be supporting some heavy bruising right about now. With a tight jaw, you glared up at him with hard and reddened eyes and awaited his threat.

“Then Sammy starts losing fingers.”

You felt the shock travel down your spine, as your face fell.

_Sam._

You knew you were going to regret it, but you couldn’t stop your eyes from traveling over to your twin.

 _God_. You wished you hadn’t.

His eyes held just as many unfallen tears as yours did not moments ago. You hated that he was seeing you like this, but you also knew that his tears weren’t just from what Dean was doing.

No, Sam knew you better than that. He knew that you wouldn’t be able to handle it if anything happened to him, especially if there was something you could do about it. That’s why your twin was crying because he knew that you’d do anything that Dean told you to do right now, as long as it would keep Sam safe.

He knew because if your places were switched, he knew that he’d do anything to protect you too.

But _damn_ , he hated it. He hated it because there wasn’t a damn thing he could do about it, and there wasn’t a damn thing you could do about it, neither.

_Damn the demon that caused this._

You felt your head being twisted back to the front, and you were greeted by Dean’s cock rubbing along your lips.

“So, what’s it gonna be, sis?” He raised an eyebrow at your kneeled form. “You gonna open wide, or do I need to start carving?”

You felt more tears trickle down your skin, as you squeezed your eyes shut tight. Your mind screamed at you not to do it, but your heart could only think about Sam. You didn’t know if you could live with yourself if he got hurt, so you opened your mouth and prepared for the worst.

A dark chuckle was all you heard before you felt him tug hard on your hair.

“You didn’t really think I was gonna do all the work here, did you?”

Your eyes slowly opened as you looked up at him. He smirked down at you before pushing the tip of his cock against your tongue.

“Show me what you can do, sis.”

Your face showed disgust and hatred, but you had no choice. With shaky nerves, you leaned in and took him further into your mouth.

“Better hope it’s up to my standards. Sammy’s limbs depend on it.”

You momentarily slowed your actions at his words before closing your eyes and continuing your motions. You soon increased speed after a few moments. A dark growl rumbled from your brother’s chest, and you prayed that he’d be quick.

Hopefully, the sooner he finished, the sooner you and your twin could escape.

For some reason, you doubted that’d be the case.

“Eyes on our sister, Sammy,” Dean commanded.

The words threw you, and you risked a glance over to your twin. He had his head turned toward the side and was gazing at the floor with a tortured expression on his face.

Of course, he wasn’t looking at you. _How could he?_

He seemed to ignore his brother’s words; possibly not even hearing them. It wasn’t until a quick thrust of Dean’s hips caused you to gag that your twin turned back.

“Same goes for you, Sammy. You don’t listen, then I stop playing nice with Y/N/N,” Dean said, as he slowly started controlling the motions of your head movement.

Sam twisted his head back to face you, and let his eyes flutter shut as he tried to hold back tears. A loud smack caused him to flinch, and he opened his eyes in time to see a red handprint forming on your cheek.

_As if the tear stains weren’t enough._

Dean’s hands suddenly trailed downward to tug at your shirt. You tried pulling away, to no avail, of course. A loud tear instantly filled the room and your shirt was thrown to the side, discarded and forgotten about. Only your bra remained to cover your top half, and you hoped that he had enough heart to let you keep some of your dignity.

_Another useless request._

The fabric tore like paper under his strength, and your breasts fell down slightly at the lack of support. You tried your best to hold your tears in.

Your twin did his best to keep his eyes on your face, and he briefly flicked his gaze up to meet Dean’s, who was wearing a smug smile and flashing dark eyes. Sam sent the best glare he could manage, but it turned out more pitiful than anything else.

Slowly moving his eyes back toward your head, your twin watched as you sucked off your older brother. Sam could see the tremble in your limbs. To any other person, even a hunter, it would’ve been mistaken for nerves, but he knew you better than that.

You were _terrified_ , but you were doing your best not to show it.

“Want the next round?” Dean’s voice rang out.

He smirked down at your kneeling form before guiding a hand to run over your cheek in a slow manner, and you almost would’ve mistaken it for tenderness, if you were any less wise.

His gaze traveled from your face over to his brother, and he raised an eyebrow. “Eh, Sammy? Want to know how good our sister can give it?”

Sam’s face instantly shifted into one of disgust, before he heard whines erupting from your mouth. He looked to see you shaking your head as best you could.

_Yeah, neither of you liked that suggestion._

“Shame. Really.” Dean mocked before he looked back down to you, and his head fell back in pleasure. “Damn, sis. You really know how to work that mouth. Maybe you are good for something after all.”

Your mind twisted at his words and you felt anger flood your veins. As if the loss of your dignity wasn’t enough, you had to listen to his degradation too.

_He really just couldn’t let up, could he?_

You were brought out of your thoughts by a sharp tug on your hair. Dean’s cock came out of your mouth, connected from the tip to your lips by a string of saliva. Your eyes traveled up to your brother’s in slight confusion at his sudden actions, only to meet an angry expression and ebony eyes.

Your attempt at displaying a tough exterior failed after hearing the growl that erupted from his throat. Your eyes cascaded downwards as your mind turned over what could have pissed him off.

_Not enough tongue? Too much? Or maybe-_

_Oh._

_Oh, God._

Your eyes widened as they landed on his cock. _There was blood. And teeth marks_.

You had bitten him.

The sound of rushing blood suddenly filled your head, and your throat dried at the sight. As the realization hit you, the faint, bitter, and burning taste of sulfur suddenly filled your mouth. You tried to spit out what remained, but you only succeeded in aiming at Dean’s pants.

As the shock soared through you, your gaze traveled from the stains on his clothing back up to meet your brother’s eyes. “I didn’t… I didn’t mean to.”

It didn’t hurt him. You knew that. Everyone knew that, but you had done something without permission. You had disobeyed, now someone was going to get the punishment for it.

Holding your breath, you anxiously awaited his reaction. His expression shifted as a wicked smirk suddenly took over his face. You were sure that you felt your heart rate increase at the sight of it, too.

“And here I was thinking that Sammy was the only one who had the hots for blood. If you wanted rough, sweetheart, all you had to do was ask.”

Before you could blink, your brother’s cock was suddenly pressed back against your mouth. You felt your breath leave you as he suddenly started the assault on the back of your throat.

Your attempts to pull back were useless. All it resulted in was Dean tightening his hands in your hair and holding you still while he fucked your throat. You felt the vile taste of his blood fill your mouth once more as he used your throat to his satisfaction. While trying to wriggle your hands free, you leaned back in retaliation.

Your brother obviously didn’t like that, as he quickly pulled you back towards him as his hips pounded against your mouth. With every thrust, your nose would be buried into his pubic hair.

His grunts and growls filled the air, accompanied by the sounds of your whines and gags.

You felt the lack of oxygen becoming too much for you, as black filled your vision and your lungs started to burn.

If you were lucky, you’d just pass out.

_But then again, God had never been that kind._

Right before you felt the dark completely envelop you, Dean pulled away and took a few steps back. Coughing and spitting up blood as you gasped for air, you leaned over in exhaustion. His growls that filled the air told you that he was close, yet he has willingly pulled away.

_Probably thought you hadn’t been humiliated enough yet._

Blinking away the dark spots, you looked up to your brother with a bruised face and saliva dripping off of your bottom lip. He stared back at you with predatory eyes, and you both held the gaze for a moment before a smirk grew on his face.

His eyes slowly traveled down your body until his gaze stopped and rested on your pants. He briefly looked back up to meet your line 0f sight, before taking a step forward. You instinctively tried to crawl away, but he moved faster than you. He kneeled down to meet you face-to-face and his hands landed on your knees.

You knew what he was thinking, and your breathing stilled as you held eye contact with him. Both of you waited for the other to make a move, but it wasn’t until the chains of your hand restraints clicked together that Dean yanked your legs out from under you.

You fell back and let out a groan of pain after landing on your tied wrists. Looking back up to him, you watched as his hands traveled up your pants to the waistline. Your breath hitched as he came closer to your core.

You let a confused expression cover your face as his hands continued upwards to graze your stomach. You tried to wriggle backward away from his touch, as his hands neared the bottom of your breasts. The sensation of his nails along your sensitive skin was almost too much to bear.

An, almost, inaudible whine left your mouth as his hands wrapped around your breasts. He gave you no time to fear what was coming, and instead immediately started pinching and pulling your nipples.

You let out painful groans at the feeling as you tried to shake him off of you. You let your eyes fall shut in another attempt to hold back tears as he toyed with your body.

_Why you? Why this?_

The sound of metal dragging on the ground brought you out of your thoughts, and you leaned your head up slightly to see the cause of the noise. Your reddened eyes widened at the sight of the knife in your brother’s hand.

“No…” You whined pitifully as he dragged the blade to the end of your pant leg.

You only heard his deep chuckle before he slowly started slicing the fabric. You felt the stinging pain travel up your leg with the motion of the weapon, and you internally cursed him for not caring if he cut you or not.

As he neared your thigh, you became antsier and prayed that he wouldn’t do what you thought he was doing.

His movements slowed as his eyes lingered on your cunt, before he continued the slice up to your waistline. The fabric of your pants soon fell to the ground on that side of your body. With a hard and tear-filled glare, you observed the thin streak of blood that lined your leg.

You flicked your eyes up to his, only to see him admiring his work with a sadistic grin. As he switched to the other side, you let your head fall back.

_Damn bastard was still hard too._

A deeper cut into your skin caused your head to shoot back up, and you looked at Dean with wide eyes. His sight was still on your leg, right where the excess of fresh blood was dripping out of your skin was.

“I told you, Sammy. _Eyes on our whore of a sister._ ” Dean growled, his voice twisting into something more sinister as he spoke.

You felt tears drip down your cheeks once more as you sniffed. With a pitiful look, you slowly turned over to your twin, who had tears of his own streaked down his face.

“You know, it’s a shame you have your soul,” Dean muttered.

He intended the words to be directed towards your brother, but his eyes were still focused on the blade moving up your leg.

“If you didn’t, maybe you’d be more willing to get a taste of the cherry pie yourself,” Dean gave an exaggerated sigh.

You grimaced at his words, and you couldn’t stop yourself from snapping, “Keep your fucked up fantasies to yourself.”

His movements stilled and you internally damned yourself for not biting your tongue. A scream of pain left your mouth as he quickly, and harshly, finished slicing up your other leg.

“Maybe you like the fucked up fantasies, sis, because you keep _mouthing off_.” Dean’s blade was instantly at your throat, and you held your breath as he glared at you.

You held your words this time before Dean finally leaned away from you. His eyes traveled down your body before landing on your pussy, which was still vaguely covered by what remained of your pants.

An evil smirk suddenly took over his face as he used his blade to slide the cut fabric to the side. Now, only your underwear remained.

Your brother eyed your covered lower legion hungrily as he laid the knife down beside him.

Before you had time to protest, his hands were on your underwear, tearing and ripping like a wild animal.

Your arms were almost numb by now, and you felt your will to fight slowly fading away.

_Damn bloodloss. What was left to fight for, again?_

A harsh grip on your bloodied ankle brought you out of your thoughts and your eyes hazily opened to see your brother staring at you with hard eyes.

“I said. _Spread. Your. Legs._ ” He commanded.

You felt the tears build once more as you shook your head.

_God. You couldn’t do that._

You refused his advances and kicked at him in retaliation. After your foot narrowly missed his crotch, he quickly stood.

Your brothers had always towered over you, but this was something else. Something worse. You couldn’t move here. You couldn’t fight back.

_Is this was all the things you hunted felt like? To be this helpless and weak in front of a Winchester?_

Your face quickly shifted into one of regret as your actions hit you. You half expected the knife to end up in your stomach as a result, or to feel your windpipe crushed underneath his hands. You watched as he walked over to grab the blade on the ground, and you instinctively tried to, unsuccessfully, ball up on the ground.

Confusion filled your face as Dean stepped over you, almost as if you weren’t even there. Then it hit you.

_Sam._

Pleads and begs left your mouth as you rolled to see Dean stride up beside his brother. Sam tried to lean away, but there was only so far he could go while being restrained.

“What did I tell you, Y/N/N? What did I say would happen if you acted out?” Dean asked as he grabbed a hold of one of Sam’s hands.

“No!” Your voice came out broken and strained, and you screamed as Sam tried to pull away.

“Dean, wait!” You yelled as Dean pressed the blade to the start of his brother’s pointer finger.

You thanked whatever godly being was watching as he stopped his movements and looked up to meet your eyes.

“Please,” You pleaded. “I’ll be good.”

Dean’s eyes flashed an obsidian color as he watched you shift positions. A smirk grew on his face as you turned over onto your stomach and proceeded to stick your ass up into the air. A deep laugh left his mouth as he threw the knife to the ground and let Sam’s hand go.

Your twin instantly recoiled his hand and grimaced at the deep mark Dean had left. It was good that his finger was still connected, but it wasn’t good that he could see bone.

“You really are desperate to keep Sammy safe, aren’t you?” Dean chuckled, as he eyed your posed backside with hungry intent. “Even if it means you take all the hits.”

“You’ve done your fair share of things to keep us safe, too,” You muttered with a shaky voice.

“Right.” A sharp slap to your ass. “Back when I was young and dumb. Now, _look at you._ ”

You heard him kneel behind you and felt the tip of his dick being rubbed through your folds.

“On your knees, face down, ass up, legs spread,” Dean mocked, still continuing the slow up-and-down movement of his member. “Your cunt practically dripping at the thought of my cock.”

You sniffed and let your eyes fall shut at his words. The ground was cold against your cheek, but at least your arms weren’t holding your weight any longer. Something told you that it didn’t matter anyway, though.

“You sure you don’t want a hole, Sammy?” Dean asked, sending a look over to his brother who quickly shook his head at the question. “Your loss.”

You let out a defeated sigh at the humiliation. You were laying on the floor of some abandoned building, about to get fucked by your demonic older brother while being watched by your twin brother.

_Yeah, this was Hell._

You felt him insert himself into your opening, and you braced for the assault that was coming but felt your breath leave you as he pulled out. A dark chuckle radiated from him as he slowly slid his dick upwards to your ass.

You stilled your movements as you felt him press against your rim. You tried wiggling your ass to discourage him, but that probably just made it worse if anything. Whines left your mouth as he slowly pushed in. The burn increased the deeper he went.

Cries left your mouth at the pain, and your brother’s grunts filled the air. What little lubrication that coated his dick from your folds was now worn off, and you were taking most of the sting. He soon started increasing his speed and you felt screams of pain get lost in your throat.

“Stop,” You begged, but your words went both unheard and uncared for.

The realization soon hit you as your body swayed. _He was going to tear you up from the inside out._

“Fuck,” Dean growled. “So tight.”

“Dean…” You whined as he slammed his hips against yours.

You felt the lightheaded feeling begin once more as your eyes started becoming unfocused. You wearily peered at the wall before feeling nails digging into your asscheeks.

He increased speed as inhuman growls left his mouth. You watched as dark spots began to cloud your vision before you felt your brother slowing his pace. You didn’t have the strength to look back.

He suddenly pulled out of you and you couldn’t bring yourself to know if he finished or not.

You heard him stand and then lean over you before grabbing ahold of your bounded wrists. You let out a small cry at the pain before you heard the snapping of metal and felt the heavy chain fall to the ground. Your arms instantly fell to the side, and you sighed at the small amount of relief.

A sudden tug backward and a push sideways on your body caused you to roll onto your side. You laid there motionlessly, as Dean smirked at your exhausted appearance. You felt him push you over once more and now you were laying on your back again.

You were finally able to see that he didn’t reach climax. His cock was still hard and waiting for release. You watched him lean down and crawl over once more, obviously intent on finishing what he started.

You didn’t have the energy to cover yourself and instead let Dean do what he wanted. He positioned his cock back against your asshole once more and you inhaled as you braced for the impact, but sighed when he moved the tip up to your pussy instead.

You knew what he was doing. Keeping you on edge. Trying to throw you off, and give you false hope.

_You hated that it was working._

“Just cum already,” You whined, tired of this game.

Dean chuckled as his eyes traveled over your bruised body. “Someone’s impatient.”

You just wanted this to be over.

You felt the tip of his cock press against your opening before pushing in. You let out a small noise at the sensation of being filled, but your brother gave you no time to adjust before he continued his thrusting.

The smell of sweat, arousal, and blood was becoming too much for you to bear. _Hopefully, you’d pass out, but you didn’t know if that was good or bad._

As soon as your eyes fluttered shut, you felt a sharp slap to your cheek. Looking up, you watched as Dean grabbed hold of your jaw and shift your head to the side. Your eyes landed on Sam’s, who stared at you pitifully before casting his glance to the ground.

You felt tears leave your eyes once more as you cried out. Your sobs, combined with the wet sounds of skin against skin, filled the air.

A deep growl filled the air, and you felt Dean grab hold of your legs and spread them further in an attempt to push deeper inside you. You turned your head back to look at him and by the feel of his throbbing cock, you could tell he was close.

You prayed he wouldn’t do it inside of you, but you knew that was too much to ask.

His hips increased speed and a hand was wrapped around your neck. You felt your breath start to give out as he tightened his grip. You whined and sobbed before you finally felt him release inside of you.

His movements slowed before stopping completely. Your eyes moved to the ceiling as you blinked back more tears. The feeling of his seed burned slightly against your walls, but that was to be expected with a demon.

You tried wiggling away from him, but you only earned yourself a dark laugh from your brother.

“I never said I would stop after I came, sis,” Dean growled, ending his sentence with a thrust of his hips.

Your face fell at his words. You held his gaze for a moment as your mind turned over his words.

_Oh, God._

Dean chuckled at the expression on your face, “We’re not done here until you’re cumming around my cock.”

You shook your head quickly and tried to scoot away, but Dean quickly grabbed hold of your ankles and pulled you back towards him. You tried using your hands to push him away or at least get a hit off, but your strength was nothing compared to his.

He smirked at your attempts to escape, and instead leaned over you as his hips picked back up speed.

As much as you hated it, you could feel an orgasm building.

You screamed and tried to maneuver out from under him, but your attempts were all useless. You wildly shook your head and refused to look at him. It wasn’t until you felt a sting along your stomach that you looked back up.

_He had a knife. He was carving something into your skin. He was—Oh—He was carving his name into your skin._

You heard Sam’s muffled shouts beside you, but they were drowned out by your own. You screamed louder at each letter, and it wasn’t until Dean threw the knife to the side and moved a hand down to circle your clit that your body began shifting.

You couldn’t take it. You were close. _He knew that._

“Come on, Y/N/N, show us how much you love it,” Dean growled as he increased speed in his motions.

You felt yourself climbing that peak, no matter how much you tried to refuse. Sounds became blurred together as spots filled your vision. You finally reached climax, only to tumble over the edge in a fit of hysteric pleasure.

_He didn’t stop._

You soon felt overstimulation take over and you cried out as pleasure turned more painful every second. Pleadings left your mouth in unintelligible sentences as you struggled to form coherent words.

After many tears, and what felt like an eternity, Dean finally relented and pulled away from you. You blinked up at him through weary eyes and squinted at his figure. You watched as he moved his cock back into his underwear and zipped back up his pants.

A sideways glance over at your twin showed his gaze set firmly on the ground.

Not that you blamed him. You probably looked like a used and abused whore right now, but that’s probably what you were.

Dean cast his eyes over your body and smirked at his work.

You didn’t have the energy to even glare or move from your position, so you instead watched as he walked over to your side and grabbed the chain off of the floor that once bound your wrists together.

He strode over to where Sam was and wrapped it around his brother’s neck before a sound of protest could occur. He pulled tightly and you watched as your twin’s face quickly began shifting in color.

You let out small begs for Dean to stop, but your attempts were useless.

“Don’t worry,” Dean said, and you watched as your twin’s eyes finally fluttered shut. “He’s still alive.”

Your brother threw the chain back to the ground and took a few steps toward you. You instantly tried to recoil, to almost no avail, and instead watched as Dean squatted near your head. He chuckled as he ran a hand over some bruises and cuts before grabbing the knife once more and running it over lightly your skin.

“You might wanna get that taken care of,” Dean teased, as he pointed to your cunt with the edge of his blade, where his cum was dripping out onto the ground. “I know how you hate the possibility of accidents happening.”

Your face shifted into a glare as he brought the weapon up to your neck.

_You should have felt nervous. You shouldn’t have felt like death would be a release._

_You just couldn’t give a damn anymore._

Dean chuckled at the blade before leaning closer to your face. His eyes flashed black and he threw the blade to the side and replaced it with his hand.

“Just kidding about the knife,” He motioned to the weapon before sending you a wink. “I could never do that to you, sis.”

You felt your breath leave you in disbelief as he stood up.

_That? After everything he just did, that was the mercy he showed you?_

You watched him walk to the doorway before stopping short.

“Y/N/N, if you and Sammy come after me again, I promise that our next time together won’t be as fun.”

That was the last thing you heard before he left.

You glanced over at Sam, who was still out cold, before letting your head fall back against the hard ground. You let out a loud cry as the events turned over in your head.

_That wasn’t mercy. If he wanted to show you mercy, then he would’ve killed you._

There wasn’t any good in him. That wasn’t Dean Winchester anymore. Or, _maybe_ it was. Maybe you just got to see him from the other side this time.

Dean Winchester really was the world’s best hunter. You were just sad that you got the worst of his act.

**Author's Note:**

> If you actually read all of that, wow. Thank you.
> 
> Let me know if you enjoyed it, please ♡


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